The Hamas attack on Israel of 7 October and the subsequent Israeli destruction of Gaza have caused several shifts in the dynamics of Israel’s occupation of the Palestinian territories, just as important continuities have remained. This mix makes scenario planning an appropriate method for analyzing the future of occupation. Scenario planning aims to unlock our mental imagination and invites us to consider different possible futures simultaneously. This helps develop a better understanding of how such futures should affect today’s decisions and improve preparedness. With this in mind, the Chapter outlines four scenarios for the future of occupation. First, a ‘Revisionist Zionism comes true’ scenario, which amounts to a fast expansion of Israeli annexation that meets only low levels of Palestinian resistance. Second, ‘Gaza on the Jordan River’ that features a similarly fast expansion of occupation but which runs into stiff Palestinian resistance. Third, ‘colonial-style suffering’ that sees a return to occupation modalities and practices from before 7 October 2023. Finally, a ‘squid game’ scenario where gradual occupation meets heavy Palestinian resistance. Even if one of these scenarios comes to pass soon, the scenario set continues to offer a mental map to inspire diplomatic engagement that intends to bring shifts between scenarios about. While the scenarios are all bleak, they are amenable to international intervention.